This is Kaito Itomura, mentor of team 8 (formed by Kiyoshi, Natsuki Hatake and Sayuki Hatake).
He was originally a close adviser for the hokage, and once was the leader of the Anbu Black Ops. Now retired, he's a mentor for newely appointed genin. Kaito is 31, male, single, a leo, and very well known for his lateness. Witty, lazy, and sarcastic, he doesn't ever seem to take things seriously. Always irritating people around him, most just think of him as a lazy good for nothing. But, constantly monitoring everything. He proves he's smarter than he looks, and a sly devil at that. Capable of tricking the enemy and wrapping them around his finger, he's the most intelligent mentor on the team. At the same time, he has a deep loyalty to those that learn to trust him in his lazy facade and he will put his life on the line for those who he cares for.
Kaito Itomura (c) Shiko Hayashi and I
timer is a liaar, i was LSing and discussing with her while drawing :3